The Investor Coaching Show with Paul Winkler

When people say “the market is down,” they may not be telling the whole story. In reality, there isn’t just one market, and the way your portfolio is diversified can make a big difference in how you experience market movement. Today, Paul explains why broad statements about the market can be misleading and how it’s easy to get confused when there are two types of diversification: diversification o...

A client calls Paul unsophisticated because he doesn't actively use a specific Social Security analysis software or push clients to do Roth conversions. The reality is that Roth conversions are a huge marketing tool for companies. Investors love the idea of making a sophisticated tax move, but Roth conversions don’t make sense in every situation. Listen along as Paul shares five compelling reasons...

It’s a common misconception in the investing industry that bigger is always better. If someone manages $85 billion in investments, shouldn’t they be a pro? Unfortunately, this is rarely the case. Today, Paul shares an interview on national television in which a Wall Street “legend” really gets pressed on his 20+ years of bad investing advice. Listen along as Paul describes what a “permabear” is in...

You go through two different phases with money in life. In the first phase, you work for money. In the second, your money begins working for you. No one wants to enter retirement only to find themselves dependent on family or the government because they weren’t prepared for that transition.   In this episode, Arlene Brown joins Paul to discuss six habits that can help you build greater financial i...

Does your adviser believe that it’s their job to make sure you’re in the “right” part of the market at the right time? Today, Paul and Jim talk about why it’s important to read through the ADV of your firm because it explains what your adviser believes their job actually is and how they will manage your money. Find someone who will not market time with your money under the code words of “tactical...

There is an entire side industry in the investing world that teaches advisers how to give free dinner workshops and presentations to make sales. Paul and Jim talk about how the industry works to emotionally manipulate you by offering something free, knowing you will feel obligated to give something in return. Listen along as these two advisers discuss a PSA from AARP about the growing number of fi...

After all the hype over SpaceX in the last few months, some investors were convinced they should break a basic investing rule and try to time the market. Today, Paul and Jim talk through the first week of SpaceX as a public company and why they believe investors should avoid trying to time the market, regardless of how compelling a company or cryptocurrency may appear. Listen along as these advise...

An investor works really hard to live off a side hustle, maximize saving, minimize spending, and retire by 25. Sounds great, right? Today, Paul and Jim challenge the idea of the FIRE (Financial Independence, Retire Early) movement and what happens when you put financial independence as your ultimate objective. Paul explains that FIRE retirees may open themselves up to a life in which they miss per...

Today, Paul shares a lot of rhetoric around why first-time homebuyers can’t get into a home. Most people think that housing regulations or lifestyle are to blame. Paul recognizes that buying a home will likely require a combination of discipline, compromise, and luck. For those thinking about buying a house for the first time, Paul shares some guidelines he would follow. Paul also explains that if...

Paul opens the show by talking about his experience in insurance sales at the beginning of his career. In these companies, advisors are taught to “smile and dial” and move products that make them and the company the most money. Listen along as Paul shares a video in which an insurance salesperson talks about LIRP and IUL plans and how he tries to sell them. Paul and Evan push back and teach you wh...

A recent headline claims Social Security could deplete its trust fund as early as 2032, leaving many retirees wondering if their benefits are at risk. In this episode, Paul and Evan separate fact from fear by breaking down what "running out of money" actually means, how Social Security is funded, and what would likely happen if the trust fund were exhausted. Paul encourages young people to get in...

SpaceX finally went public, and investors everywhere are wondering the same thing: "Should I have invested in the IPO?" If you didn’t get in on SpaceX (SPCX) on Friday, don't worry — you may have dodged a bullet. Listen along as these two advisors discuss how impossible it is for the market to evaluate a company like this properly, the data we have on IPO performance, and why a confident investor...

What happens when an asset's value depends entirely on what someone else is willing to pay? In this episode, Paul breaks down the key differences between investing in stocks and owning commodities like Bitcoin. He explains why stocks are backed by the earnings power of companies, while commodities rely on supply, demand, and investor sentiment. You'll also hear how a single influential voice can s...

Most people picture retirement as something they'll choose on their own terms. But what if life has other plans? In this episode, Paul examines why many people end up working longer than they expected, while others leave the workforce earlier than they planned. From health issues to family obligations, retirement timing is often influenced by factors beyond our control. Learn why preparing now — n...

The SpaceX IPO is already upside down. SpaceX's valuation would place it among the largest companies in the S&P 500, yet its revenue tells a very different story. In this episode, Paul explains how buying an IPO is fundamentally different from trading other stocks in the market and what that matters for investors. Later in the episode, Paul wants you to know how to spot a market “forecast” and...

Not all financial planners provide advice that aligns with your goals. In this episode, Paul shares lessons from 30 years in the gym and explains how the right weight coach can help you avoid mistakes, uncover blind spots, and reach your goals faster. He discusses why the same principles apply to money and investing and how the right guidance can help you become a more confident, successful invest...

Robinhood has made a fortune from selling the idea of day trading and gambling to investors. Today, Paul and Jim talk about the most recent move Robinhood has made to allow you to connect your account to an AI trader who will make investment decisions for you. Listen along as these two advisors discuss why they believe this is one of the worst ideas they’ve heard to date and how a company can get...

If timing the market truly works, then why doesn’t anyone agree on when you should get in or get out? Today, Paul brings a blatant example of market timing advice that many investors fall for because they believe they’re listening to an expert. Listen along as these two advisors discuss all the most common market timing strategies people try, even though none of them are proven to work for any mea...

Why are billionaires becoming the centerpiece of so many political conversations? In this episode, Paul and Jim explore the economic ideas often left out of the debate. They discuss how wealth creation, incentives, and entrepreneurship have contributed to longer life expectancies and higher standards of living worldwide. They also explain why financial literacy matters more than ever and share a r...

Today, Paul and Jim break down an interview in which two financial media pundits correctly inform investors that having too much in large U.S. tech companies is risky, but then claim the fix is to invest in private equity and commodities. Listen along to hear why Paul and Jim disagree with these proposed solutions that ignore the research suggesting these areas may introduce uncompensated risk to...

From SpaceX to OpenAI, IPOs are dominating the news cycle right now. Today, Paul and Evan share why IPOs look so exciting and how they entice investors to invest emotionally because they appeal to your desire to avoid missing out on the companies and technology of the future. Listen along as these two advisors explain why IPOs like SpaceX and OpenAI sound like incredible investments and reveal the...

Today, Paul and Evan continue their conversation about getting educated and understanding how to be a confident investor in retirement. Listen along as these two advisors discuss whether or not to put your money in a Roth or traditional IRA and explain some of the rules around taking an income in retirement that maximizes the money that you worked so hard to earn in your earning years. Later in th...

This week, Paul watched a video from another advisor in which he attempts to condense 30 years of investing lessons into 20 minutes. Getting educated is important, but it’s not a quick process. Paul Winkler, Inc. has worked for decades to create confident investors through education. Listen along as Paul and Evan cover a few fundamental retirement concepts and discuss predicting your income with i...

This week, Paul watched a video from another advisor in which he attempts to condense 30 years of investing lessons into 20 minutes. Getting educated is important, but it’s not a quick process. Paul Winkler, Inc. has worked for decades to create confident investors through education. Listen along as Paul and Evan cover a few fundamental retirement concepts and discuss predicting your income with i...

The draw for many crypto investors has been owning something that isn’t tied down to any specific government or bank. Now in 2026, the U.S. moves aggressively to implement sweeping regulation over these digital assets. Today, Paul and Dan address a question on many crypto investors' minds: Will regulation add to the value of crypto or completely defeat its purpose? Listen along to hear why a more...